Abstract
5-(3-Thienyl)-10,15,20-triethyl-21H,23H-porphine was prepared by the ring closure of pyrrole and a 3:1 mixture of propionaldehyde and 3- thiophenecarbaldehyde. Oxidative polymerization of the porphyrin with typical oxidants such as FeCl3 gave a polythiophene derivative bearing porphyrins directly bound to the β-position of the main chain. The very bulky β-substituents allowed the polymerization to proceed regioselectively even at room temperature, resulting in the formation of the β-substituted polythiophene with an HT-HT content of more than 90%. The porphyrin substituents aligned cofacially along the main chain, which served as the catalytic site for the four-electron reduction of O2 to H2O (O2 + 4e- + 4H+ = 2H2O) when cobalt ions were introduced into the porphyrins. A novel platinum-free catalyst for the reduction of O2 for fuel cell cathodes, 1/CB (M = CoII), was thus prepared by the electropolymerization of the porphyrin at the surface of carbon black (CB), which reduced O2 with four electrons at more poritive potentials than the standard two-electron reduction potential of O2 to H2O2.
| Original language | English |
|---|---|
| Title of host publication | Polymer Preprints, Japan |
| Pages | 3030-3031 |
| Number of pages | 2 |
| Volume | 55 |
| Edition | 2 |
| Publication status | Published - 2006 |
| Externally published | Yes |
| Event | 55th Society of Polymer Science Japan Symposium on Macromolecules - Toyama Duration: 2006 Sep 20 → 2006 Sep 22 |
Other
| Other | 55th Society of Polymer Science Japan Symposium on Macromolecules |
|---|---|
| City | Toyama |
| Period | 06/9/20 → 06/9/22 |
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Keywords
- Conjugated polymer
- Electrode catalyst
- Electron transfer
- Polymer complex
- Porphyrin
ASJC Scopus subject areas
- Engineering(all)
Cite this
Synthesis of structure-defined conjugated polymers directly bound to porphyrins. / Oyaizu, Kenichi; Hoshino, Manabu; Imai, Takuya; Murata, Hidenori; Yuasa, Makoto.
Polymer Preprints, Japan. Vol. 55 2. ed. 2006. p. 3030-3031.Research output: Chapter in Book/Report/Conference proceeding › Conference contribution
}
TY - GEN
T1 - Synthesis of structure-defined conjugated polymers directly bound to porphyrins
AU - Oyaizu, Kenichi
AU - Hoshino, Manabu
AU - Imai, Takuya
AU - Murata, Hidenori
AU - Yuasa, Makoto
PY - 2006
Y1 - 2006
N2 - 5-(3-Thienyl)-10,15,20-triethyl-21H,23H-porphine was prepared by the ring closure of pyrrole and a 3:1 mixture of propionaldehyde and 3- thiophenecarbaldehyde. Oxidative polymerization of the porphyrin with typical oxidants such as FeCl3 gave a polythiophene derivative bearing porphyrins directly bound to the β-position of the main chain. The very bulky β-substituents allowed the polymerization to proceed regioselectively even at room temperature, resulting in the formation of the β-substituted polythiophene with an HT-HT content of more than 90%. The porphyrin substituents aligned cofacially along the main chain, which served as the catalytic site for the four-electron reduction of O2 to H2O (O2 + 4e- + 4H+ = 2H2O) when cobalt ions were introduced into the porphyrins. A novel platinum-free catalyst for the reduction of O2 for fuel cell cathodes, 1/CB (M = CoII), was thus prepared by the electropolymerization of the porphyrin at the surface of carbon black (CB), which reduced O2 with four electrons at more poritive potentials than the standard two-electron reduction potential of O2 to H2O2.
AB - 5-(3-Thienyl)-10,15,20-triethyl-21H,23H-porphine was prepared by the ring closure of pyrrole and a 3:1 mixture of propionaldehyde and 3- thiophenecarbaldehyde. Oxidative polymerization of the porphyrin with typical oxidants such as FeCl3 gave a polythiophene derivative bearing porphyrins directly bound to the β-position of the main chain. The very bulky β-substituents allowed the polymerization to proceed regioselectively even at room temperature, resulting in the formation of the β-substituted polythiophene with an HT-HT content of more than 90%. The porphyrin substituents aligned cofacially along the main chain, which served as the catalytic site for the four-electron reduction of O2 to H2O (O2 + 4e- + 4H+ = 2H2O) when cobalt ions were introduced into the porphyrins. A novel platinum-free catalyst for the reduction of O2 for fuel cell cathodes, 1/CB (M = CoII), was thus prepared by the electropolymerization of the porphyrin at the surface of carbon black (CB), which reduced O2 with four electrons at more poritive potentials than the standard two-electron reduction potential of O2 to H2O2.
KW - Conjugated polymer
KW - Electrode catalyst
KW - Electron transfer
KW - Polymer complex
KW - Porphyrin
UR - http://www.scopus.com/inward/record.url?scp=33846135058&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33846135058&partnerID=8YFLogxK
M3 - Conference contribution
VL - 55
SP - 3030
EP - 3031
BT - Polymer Preprints, Japan
ER -